KR20030090769A - Synergistic herbicide comprising benzoylcyclohexanediones for application in rice cultivation - Google Patents

Abstract

The present invention provides manufacturability comprising (A) at least one compound from the benzoylcyclohexanedione group, and (B) at least one compound from the group of herbicides that selectively act on monocotyledonous and / or dicotyledonous harmful plants in rice. It relates to a composition. These compositions show good activity compared to herbicides used individually.

Description

SYNERGISTIC HERBICIDE COMPRISING BENZOYLCYCLOHEXANEDIONES FOR APPLICATION IN RICE CULTIVATION}

Herbicides from the aforementioned benzoylcyclohexanedione groups are known in many literatures. For example, herbicidal action in many of these compounds is described in WO 98/29406, WO 00/21924 and WO 01/07422. Some benzoylcyclohexanediones mentioned in WO 00/21924 exhibit good herbicidal action against harmful plants growing in rice crops.

However, when benzoylcyclohexanedione known in the literature is used, there are often problems in practical terms. Therefore, the herbicidal activity of the known compounds is not necessarily sufficient, and even when the herbicidal activity is sufficient, undesirable damage to rice plants is observed.

The activity of herbicides depends on the type of herbicide used, the rate of application, the recipe, the harmful plants to be controlled, climatic conditions and soil conditions. Another criterion is the duration or rate of degradation of the herbicide. Where appropriate, changes in the sensitivity of harmful plants to the active ingredient, which may occur in prolonged use or within geographically defined areas, may also be considered. This change results in some apparent loss of activity, which can be compensated by a certain degree by increasing the rate of application of herbicides.

Since there are a number of factors that can affect, there is virtually no single active ingredient with desirable properties for a variety of uses, particularly for hazardous plant species and for use with climate zones. In addition, fewer and more herbicide ratios are required to achieve this effect. This small proportion not only reduces the amount of active ingredient required for spreading, but also generally reduces the amount of formulation aid required. This reduces the financial investment and improves the economic-friendly nature of the herbicide treatment.

A commonly used method of improving the usability of herbicides is to combine the active ingredient with one or more other active ingredients which contribute to the desired further properties. However, when multiple active ingredients are used in combination, physical phenomena and biological incompatibilities such as lack of stability of co-formulation, degradation of the active ingredient, or antagonism of the active ingredient often occur. On the other hand, a combination of active ingredients which exhibits a high range of activities with a beneficial range of activity of the highest synergistically enhanced activity possible is preferred as it allows for a reduced sparging rate compared to the application of the combined active ingredients separately.

WO 97/48275 discloses 2- (4-methylsulfonyl-2-nitrobenzoyl) -1,3-cyclohexanedione with nicosulfuron, rimsulfuron, thifensulfuron-methyl, primisulfuron Herbicidal mixtures of sulfonylureas selected from the group consisting of -methyl, prosulfuron and halosulfuron are disclosed. However, these mixtures also cause severe damage to rice plants and are therefore not suitable for rice cultivation.

The present invention relates to the technical field of crop protection products which can be used against undesirable plants and which comprise a combination of two or more herbicides as active ingredients.

More specifically, the present invention relates to herbicidal compositions for use in rice which comprise, as active ingredient, a herbicide from the benzoylcyclohexanedione group as a combination with one or more additional herbicides.

It is an object of the present invention to provide a rice cultivated herbicidal composition exhibiting improved properties compared to the prior art. The present invention relates to a herbicidal composition comprising the following components (A) and (B) in a weight ratio of 1: 200 to 200: 1:

(A) at least one compound of formula (I) or an agriculturally common salt thereof:

[Wherein,

R ¹ is C ₁ -C ₄ -alkyl;

R ² is OR ⁶ , SO _m R ⁷ , cyanato, cyano, thiocyanato or halogen;

R ³ and R ⁴ are independently hydrogen, halogen, C ₁ -C ₄ -alkyl, halogen-C ₁ -C ₄ -alkyl, cyano, nitro or SO _m R ⁷ ;

R ⁵ is O— (CH ₂ ) _a —O— (CH ₂ ) _b —OR ⁷ , C ₃ -C ₈ -cycloalkyloxy, C ₃ -C ₈ -cycloalkyl-C ₁ -C ₄ -alkyloxy, 2-tetrahydrofuranylmethoxy, 3-tetrahydrofuranylmethoxy, 2-tetrahydro-2H-pyranylmethoxy, 2-tetrahydrothienylmethoxy, 2-furanylmethoxy or 2-thienylmethoxy;

R ⁶ is hydrogen, C ₁ -C ₄ -alkyl or halogen-C ₁ -C ₄ -alkyl;

R ⁷ is C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, halogen-C ₁ -C ₄ -alkyl, halogen-C ₂ -C ₄ -alkenyl or Halogen-C ₂ -C ₄ -alkynyl;

n is 0, 1, 2, 3, 4, 5 or 6;

m is 0, 1 or 2;

a is 2, 3 or 4;

b is 2, 3 or 4]

(B) 2,4-D (B1.1), benzobicyclon (B2.1), benzofenap (B3.1), bifenox (B4.1), car Cafenstrole (B5.1), chlorimuron-ethyl (B6.1), cynmethylin (B7.1), dimuron (B5.2), Dimethametryn (B8.1), dithiopyr (B5.3), etobenzamide (B9.1), pentrazamide (B5.4), and Indanofan (B10.1), MCPA (B1.2), oxadiazon (B4.2), piperophos (B5.5), pyrazosulfuron-ethyl (B6.2), pyributicarb (B11.1), pyriftalide (NOJ-100) (B12.1), pyriminobac-methyl (B6.3) ), One or more herbicide compounds selected from the group consisting of propoxydim (B13.1) and quinoclammin (B14.1).

Preferred compositions are those in which the weight ratio of the compound of formula (I) or salts thereof (component (A)] and (B) [component (B)] is from 1:20 to 20: 1.

In the general formula (I) and in all the formulas mentioned hereafter, the chain carbon containing radicals (e.g. alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio) and the corresponding unsaturated radicals and / or radicals substituted in the carbon skeleton ( For example, alkenyl and alkynyl) may in each case be straight or branched chain. In addition, alkyl radicals in a complex sense such as alkoxy, haloalkyl and the like are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl. Alkenyl and alkynyl radicals have the same meaning as unsaturated radicals possible in alkyl radicals; Alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3 -En-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; Alkynyl is, for example, propazyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Multiple bonds may be located at any desired position in these unsaturated radicals.

Cycloalkyl is a carbocyclic saturated ring system, for example cyclopropyl, cyclopentyl or cyclohexyl.

Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl and haloalkenyl are alkyl, alkenyl or alkynyl, each of which is partially or completely substituted by halogen, preferably fluorine, chlorine and / or bromine, in particular fluorine and / or chlorine (eg CF ₃ , CHF ₂ , CH ₂ F, CF ₃ CF ₂ , CH ₂ FCHCl, CCl ₃ , CHCl ₂ and CH ₂ CH ₂ Cl); Haloalkoxy is, for example, OCF ₃ , OCHF ₂ , OCH ₂ F, CF ₃ CF ₂ O, OCH ₂ CF ₃ and OCH ₂ CH ₂ Cl; Haloalkenyl is similar.

Depending on the type and linkage of the substituents, the compounds of formula I may exist as stereoisomers. For example, when one or more alkenyl groups are present, diastereomers may be produced. For example, when one or more asymmetric carbon atoms are present, enantiomers and diastereomers can be generated. Stereoisomers can be obtained from the mixture obtained at the time of manufacture by conventional separation methods, for example by chromatographic separation. Likewise, stereoisomers can be prepared selectively by using stereoselective reactions and optically active starting materials and / or adjuvants. In addition, the present invention relates to all stereoisomers and mixtures thereof included in the formula (I), but is not particularly limited thereto.

Preferred herbicidal compositions are, as component (A),

R ¹ is methyl;

R ² is OR ⁶ ;

R ³ and R ⁴ are independently hydrogen, chlorine, fluorine, methyl, trifluoromethyl, cyano, nitro or SO ₂ R ⁷ ;

R ⁶ is hydrogen;

R ⁷ is methyl or ethyl;

n is 0, 1 or 2;

m, a and b each comprises 2 compounds of formula (I).

Furthermore, as component (A), R ⁵ is O- (CH ₂ ) _a -O- (CH ₂ ) _b -OR ⁷ , C ₃ -C ₈ -cycloalkyloxy, C ₃ -C ₈ -cycloalkyl-C ₁ Preferred are herbicidal compositions comprising a compound of formula (I) above, which is -C ₄ -alkyloxy or 2-tetrahydrofuranylmethoxy.

Also preferred are herbicidal compositions comprising, as component (A), a compound of formula (Ia):

Preferred substances as component (B) include herbicides benzobicyclo, benzophenaf, biphenox, carfenstrol, cinmethyllin, dimethamethrin, dithiopyr, etobenzamide, pentrazamide, indanopan, oxa Diazone, piperophos, pyributicab, pyriphthalide, pyriminobac-methyl and quinoclamin.

Particularly preferred herein are herbicides carfenstrol, dithiopyr, etobenzamide, pentrazamide, indanophan, oxadione, pyributicab, pyriphthalide, pyriminobac-methyl and quinocamine.

Active ingredients with the common names as described above are known, for example, from "The Pesticide Manual", 12th Edition, 2000, British Crop Protection Council, or as shown in the following table:

Of particular interest to the herbicidal compositions herein are one or more of the following combinations of two compounds [(A) + (B)] that exhibit synergistic activity:

In the combination according to the invention, the application rate (ai / ha) of the required active ingredient (components (A) and (B)) per ha is respectively 1 to 2000 g, preferably 10 to 500 g and 1 to 2000 g, preferably Preferably from 1 to 500 g.

The weight ratio (A) :( b) of the components used can be varied in a wide range. The quantitative ratio is preferably 1:50 to 500: 1, in particular 1:20 to 50: 1. The optimum weight ratio depends on the sparge range, weed range and the combination of active ingredients to be used and can be determined in preliminary experiments.

The composition according to the invention is very suitable for the selective control of harmful plants in rice cultivation.

The composition according to the invention can be used in all methods of spraying customary for rice herbicides. They are particularly advantageously used in the form of spray spraying and submerged spraying. Paddy water, as it is known as in-water spraying, already has a depth of 30 mm or less above the soil at the time of spraying. The composition according to the invention is added directly to this paddy water, for example in the form of granules. Globally, spray spraying is used mainly for sown rice, and the use of spraying in water is known mainly for transplanted rice.

The composition according to the invention acts over a wide range of weeds. For example, they are one year old and perennial harmful plants, for example, Abu epothilone (Abutilon), Alor pekyu Russ (Alopecurus), ABE or (Avena), Keno podium (Chenopodium), Shino money (Cynodon), Cypher Ruth (Cyperus ), Digitaria , Echinochloa , Elymus , Galium , Ipomoea , Lamium , Matricaria , Skirpus (Scirpus), theta Ria (Setaria), Broken sword (Sorghum), Veronica (Veronica), viola (viola) and Xanthi Stadium (Xanthium), in particular Echinacea furnace enclosure Ah species (Echionochloa spp.), repto claws ah species ( Leptochloa spp. ), Scirpus spp. , Cyperus spp. , Sagittaria spp. , Monochoria spp. , Lindernia spp. .), one Leo is suitable for controlling the Charis species (Eleocharis spp.) and access Vania species (Sesbania spp.).

In addition, in the herbicidal composition according to the present invention, since the effective spraying amount of the components (A) and (B) used in the combination is reduced compared to the amount when used individually, the required ratio of the active ingredient can be reduced. Differentiate from

The present invention also relates to a method for controlling undesirable vegetation, comprising the step of spraying one or more herbicides (A) with one or more herbicides (B) onto harmful plants, their plant parts or in cultivated areas.

Synergistic effects are observed when herbicides of type (A) and (B) are sprayed jointly. The activity of the combination is greater than expected combining the activity of herbicides individually and the activity of each individual herbicide (A) and (B). This synergistic effect reduces the spread rate, controls a broad range from broadleaf weeds to grass weeds, provides faster onset of herbicidal action, extended duration of activity, and uses only one or less spreads Good control of plants and extension of the spreading cycle. This property is required for weed control to separate agricultural crops from undesired competing plants, providing protection and increasing yield in terms of quality and yield. These novel combinations with regard to the aforementioned properties can greatly exceed technical standards.

The combination of the active ingredients according to the invention is present as a formulation in which the components (A) and (B) are mixed together with additional conventional formulation adjuvants as necessary and sprayed in a conventional manner in the form of diluents with water. Alternatively, all or some of the components may be separated and prepared by co-diluting the formulated components with water (known as “tank mix”).

Component (A) and component (B) can be formulated in a variety of ways depending on the prevailing biological and / or physicochemical parameters. Examples of possible suitable formulations include, but are not limited to, wet powder (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions such as heavy oil emulsions and water-in-oil emulsions, spray solutions or emulsions, oil-based or aqueous dispersions, Suspoemulsion, dust (DP), seed-dressing products, disperse and soil spray granules, water dispersible granules (WG), ULV formulations, microcapsules and waxes.

These individual formulation types are known in principle and are described, for example, in Winnacker-Kuchler, "Chemische Technologie" [Chemical Engineering], Volume 7, C. Hauser Verlag Munich, 4th Ed. 1986; van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London. Necessary formulation auxiliaries such as inactive ingredients, surfactants, solvents and further additives are likewise known and described, for example, in Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1950; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N. J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte" [Surface-actvie ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Kuchler, "Chemische Technologie", Volume 7, C. Hauser Verlag Munich, 4th Ed 1986.

Based on the formulation, for example in the form of pre-mixing or tank mixing, combinations of emollients, fertilizers and / or growth regulators with other pesticidal active ingredients such as, for example, insecticides, tick insecticides, herbicides and fungicides It can also manufacture.

Wettable powders are homogeneously dispersible in water and, in addition to the active ingredient, include, in addition to diluents or inerts, ionic and / or nonionic surfactants (wetting agents and dispersants) such as polyoxyethylated alkylphenols, polyoxyethylated Fatty alcohol, fatty amine, fatty alcohol polyglycol ether sulfate, alkanesulfonate, alkylbenzenesulfonate, sodium lignosulfonate, sodium 2,2'- dinaphthylmethane-6,6'-disulfonate, sodium di Butylnaphthalenesulfonate or other sodium oleoylmethyltaurate.

Emulsifiable concentrates, for example, dissolve the active compound in an organic solvent of butanol, cyclohexanone, dimethylformamide, xylene or other high boiling aromatic compounds or hydrocarbons, and at least one ionic and / or nonionic surfactant. It is prepared by adding (emulsifier). Examples of emulsifiers that can be used are calcium alkylarylsulfonates (eg calcium dodecylbenzenesulfonate), or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, Propylene oxide / ethylene oxide condensation products, alkyl polyethers, sorbitan esters (eg, polyoxyethylene sorbitan fatty acid esters), or polyoxyethylene sorbitan esters.

Dust is obtained by grinding the active ingredient together with finely divided solid materials, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

The granules may be sprayed with an adhesive, for example polyvinyl alcohol, sodium polyacrylate or other mineral oil, to spray the active ingredient onto the adsorptive granulating inert ingredient or the active ingredient concentrate to a carrier such as sand, kaolinite or granulating inert ingredient. It can manufacture by spraying on the surface of. Suitable active ingredients can also be granulated in a manner customary for the preparation of fertilizer granules, optionally as a mixture with fertilizers. Water dispersible granules are generally prepared by methods such as spray drying, fluid bed granulation, disc granulation, mixing and extrusion using a high speed stirrer, without the use of solid inert ingredients.

Pesticide formulations generally comprise from 0.1 to 99% by weight, in particular from 0.2 to 95% by weight, of active ingredients (A) and (B), wherein the concentration of the active ingredient in the wettable powder is for example from about 10 to 95% by weight and 100% by weight of the remainder consisting of conventional formulation components. In emulsifiable concentrates, the concentration of the active ingredient can be, for example, from 5 to 80% by weight. The formulations in dust form comprise 5-20% by weight of the active ingredient and the spray solution contains about 0.2-25% by weight of the active ingredient. In the case of granules such as water dispersible granules, the content of the active ingredient depends in part on whether the active compound is in liquid or solid form and the granulation aids, fillers and the like used. In water dispersible granules, the content of the active ingredient is 10 to 90% by weight. In addition, in some cases, the formulation of the active ingredient may in each case, for example, a tackifier, wetting agent, dispersant, emulsifier, penetrant, cryoprotectant, solvent, filler, colorant, carrier, colorant, antifoam, evaporation inhibitor and pH and viscosity And modulators.

For use, formulations present in commercially available form are diluted, in the case of wettable powders, emulsifiable concentrates, dispersions and water dispersible granules, if desired using conventional methods such as water. Formulations in the form of dust, soil granules, spray granules and spray solutions are usually not further diluted with other inert ingredients prior to use.

The active ingredient may be sprayed on plants, plant parts, plant seeds or arable land (cultivated soil), preferably green plants and plant parts and further arable soil as required.

One possible use is the co-spraying of the active ingredients in the form of a tank mixture, in which the optimally formulated concentrated formulation of the individual active ingredients is co-mixed with water in the tank and the spray mixture obtained is sparged.

The herbicidal co-formulation of the combinations according to components (A) and (B) of the invention has the advantage that they are very easy to use because the amounts of the components are already present in the correct proportions. In addition, the adjuvant in the formulation may be combined to optimally match each other, but different formulations may be tank mixed to produce an undesirable adjuvant combination.

A. Formulation Examples

(a) Dust (WP) is obtained by mixing 10 parts by weight of the active ingredient / active ingredient mixture and 90 parts by weight of talc as the inactive ingredient and milling the mixture in a hammer mill.

(b) Wettable powder (WG) which is easily dispersed in water comprises 25 parts by weight of the active ingredient / active ingredient mixture, 64 parts by weight of kaolin-containing quartz as inactive ingredient, 10 parts by weight of potassium lignosulfonate, and sodium as the wetting agent and dispersant. 1 part by weight of oleoylmethyltaurate is mixed and obtained by grinding in a pinned-disk mill.

(c) Disperse concentrates readily dispersed in water include 20 parts by weight of active ingredient / active ingredient mixture, 6 parts by weight of alkylphenol polyglycol ether (Triton X 207), isotridecanol polyglycol ether (8 EO ) 3 parts by weight and 71 parts by weight of paraffinic mineral oil (boiling range, for example about 255 to 277 ° C.) and obtained by grinding the mixture into a powder of less than 5 μm in a friction ball mill.

(d) Emulsifiable concentrate (EC) is obtained from 15 parts by weight of active ingredient / active ingredient mixture, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier.

(e) The water-dispersible granules are mixed with 75 parts by weight of the active ingredient / active ingredient mixture, 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin, and this mixture Is obtained by grinding in a pinned disk mill and spraying over water as granulation fluid to granulate the powder in a fluidized bed.

(f) The water-dispersible granules are 25 parts by weight of the active ingredient / active ingredient mixture, 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, and 2 parts by weight of sodium oleoylmethyltaurate. , 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water are homogenized and prepulverized on a colloidal mill, and subsequently the mixture is ground in a bead mill, granulated and the resulting suspension is a single-material nozzle By drying in a spray tower.

B. Biological Examples

1. Herbicide before germination

Seeds or roots of monocotyledonous and dicotyledonous harmful plants are placed in potted sand loam and covered with soil. For spray spraying, the compositions formulated in the form of concentrated aqueous solutions, wettable powders or emulsion concentrates are then applied onto the covered soil surface at varying spraying volumes of 600 to 800 liter spray rate (converted) per aqueous solution, suspension or emulsion, respectively. Spray. After several days of spraying, pour water into the test vessel to a depth of 30 mm or less above the soil surface. On the other hand, in the case of in-water spraying, the soil in the test container closed at the time of spraying is already covered with paddy water to a depth of 30 mm. To this, the formulated active ingredient is added directly to the paddy water, for example in the form of granules. After this treatment, the pots are placed in a greenhouse and kept under good growing conditions in the weeds. After a 3 to 4 week experimental period, the adverse effects on plant damage or sprouting after the test plants are germinated are evaluated by visual comparison with untreated controls. As can be seen from the test results, the composition according to the present invention exhibits significant pre-emergence herbicidal activity over a wide range from grass weeds to broadleaf weeds. As a result, the effect of the other combinations on the present invention is observed to be greater than the combined effect of the application of herbicides separately. When using moderately low sparse doses, the values observed in the experiments show that the effects of the combination exceed the expectations calculated using Colby's equation.

Record and evaluate herbicidal synergy:

The herbicidal efficacy of the active ingredient or active ingredient mixture is evaluated by visual comparison of the treated and untreated controls. Assess damage and improvements to all airborne organisms. Evaluation is performed in% grade (100% activity = all plants die; 50% activity = 50% of plants and green plant parts die; 0% activity = no identifiable activity = same as untreated control).

2. Herbicide after germination

Seeds and roots of monocotyledonous and dicotyledonous weeds were placed in potted sand loam and covered with soil, and then grown in a greenhouse under good growth conditions (temperature, atmospheric humidity, water supply). About three weeks after planting, the experimental plants are treated with the composition according to the invention. In the case of spray spraying, the compositions according to the invention formulated in the form of wettable powders or emulsified concentrates are sprayed onto the green plant parts in various spraying doses of 600 to 800 liter spraying rate per ha. After several days of spraying, pour water into the test vessel to a depth of 30 mm or less above the soil surface. On the other hand, in submerged spraying, the soil in the test container closed at the spraying point is already covered with paddy water to a depth of 30 mm. To this, the formulated active ingredient is added directly to the paddy water, for example in the form of granules. Experimental plants are maintained for an additional three to four weeks in a greenhouse under optimal growth conditions, and then the herbicidal effect is evaluated by visual comparison with the untreated control. The composition according to the present invention exhibits high herbicidal activity over a wide range from grass weeds after budding to broadleaf weeds. As a result, the effect of the combination according to the invention is observed to be greater than the sum of all the effects when the herbicides are sprayed individually. When using moderately low sparse doses, the values observed in the experiments show that the effects of the combinations exceed expectations calculated using Colby's equation.

3. Herbicidal activity and cultivated plant tolerance (cultivation experiments)

Cultivated plants were grown open under natural arable conditions to plant seeds or roots of typical noxious plants and to develop natural weed flora. After germination of harmful plants and cultivated plants, treatment with the composition according to the invention is carried out by spraying or spraying in water, usually in a stage of 2 to 4 leaves; In some cases (as described above), individual active ingredients or combinations of active ingredients are sprayed prior to budding or partially as a continuous treatment before and / or after budding. For example, 2, 4, 6 and 8 weeks after sparging, the manufacturing effect is visually assessed compared to the untreated control (see Example 1). In addition, the compositions according to the invention exhibit synergistic herbicidal activity over a wide range from grass weeds to broadleaf weeds, which are economically important in arable experiments. By comparison, it has been found that the combinations according to the invention are larger in most cases and in some cases significantly larger than the sum of the activities of the individual herbicides, which means that a synergistic effect has occurred. In contrast, the cultivated plants were not harmed or substantially harmed as a result of the treatment of the herbicidal composition.

When spraying the composition according to the invention, the herbicidal effect on the harmful plant species is observed to be greater than the sum of all of the effects of the herbicide when sprayed with the herbicide itself per se. Alternatively, it is observed that in some cases herbicidal combinations require less spreading rates compared to individual products in obtaining the same effect on harmful plants. This increased or decreased sparse rate of activity or potency strongly asserts that synergy has occurred. If the results already observed are larger than the sum of the results of the individual sprayed experiments, the results are likewise larger than the expectations calculated by the following Colby's equation, which asserts that a synergistic effect has occurred (SR Colby; in Weeds 15 (1967) pp.20 to 22):

Where

A and B are the activities (%) of components (A) and (B) at the spraying amounts (ag / ha) of ag and bg, respectively,

E is the expected value (%) at the spraying dose (ai / ha) of (a + b) g.

The results observed in the experimental example described above exceed expectations calculated using Colby's equation.

Examples (BI) to (B.XVII) were carried out using the method (B.2) (herbicidal weeding action) described above, and in Examples (BI) to (BV) spray spraying was used, In (B.VI) to (B.VII) spraying in water was used.

In the examples the following test plants were used:

CHEAL Kenopodium album

CYPSE Cyperus serotinus

ECHCG Echinochloa crus galli

SAGPY Sagittaria pygmaea

SCPJU Scirpus juncoides

SEBEX Sesbania exaltata

Example B.I

compound Spray amount [g ai / ha] CHEAL Measure Colby's E value A1 10 25% B6.2 10 10% A1 + B6.2 10 + 10 75% 33%

Example B.II

compound Spray amount [g ai / ha] ECHCG SEBEX Measure Colby's E value Measure Colby's E value A1 20 15% 15% B1.1 100 50% 45% A1 + B1.1 20 + 100 73% 58% 85% 53%

Example B.III

compound Spray amount [g ai / ha] ECHCG SEBEX Measure Colby's E value Measure Colby's E value A1 20 35% 15% B8.1 100 25% 50% A1 + B8.1 20 + 100 55% 51% 98% 58%

Example B.IV

compound Spray amount [g ai / ha] ECHCG CYPES Measure Colby's E value Measure Colby's E value A1 20 15% 15% B13.1 20 30% 0% A1 + B13.1 20 + 20 70% 41% 30% 15%

Example B.V

compound Spray amount [g ai / ha] ECHCG SEBEX Measure Colby's E value Measure Colby's E value A1 20 15% 15% B14.1 500 0% 0% A1 + B14.1 20 + 100 45% 25% 30% 15%

Example B.VI

compound Spray amount [g ai / ha] SCPJU SAGPY Measure Colby's E value Measure Colby's E value A1 37.5 30% 70% B2.1 75 30% 0% A1 + B2.1 37.5 + 75 80% 51% 100% 70%

Example B.VII

compound Spray amount [g ai / ha] SCPJU SAGPY Measure Colby's E value Measure Colby's E value A1 7537.5 50% 70% B3.1 30075 0% 0% A1 + B3.1 75 + 300 37.5 + 75 90% 50% 100% 70%

Example B.VIII

compound Spray amount [g ai / ha] SCPJU SAGPY Measure Colby's E value Measure Colby's E value A1 7537.5 50% 70% B5.1 75150 0% 0% A1 + B5.1 75 + 7537.5 + 150 80% 50% 90% 70%

Example B.IX

compound Spray amount [g ai / ha] SCPJU SAGPY Measure Colby's E value Measure Colby's E value A1 7537.5 50% 70% B7.1 1530 0% 0% A1 + B7.1 75 + 1537.5 + 30 80% 50% 100% 70%

Example B.X

compound Spray amount [g ai / ha] SAGPY CYPSE Measure Colby's E value Measure Colby's E value A1 37.575 70% 40% B5.2 300750 0% 0% A1 + B5.2 37.5 + 7575 + 750 100% 70% 80% 40%

Example B.XI

compound Spray amount [g ai / ha] SCPJU SAGPY Measure Colby's E value Measure Colby's E value A1 7537.5 50% 70% B5.3 15 0% 0% A1 + B5.3 75 + 1537.5 + 15 80% 50% 100% 70%

Example B. XII

compound Spray amount [g ai / ha] SCPJU SAGPY Measure Colby's E value Measure Colby's E value A1 7537.5 50% 70% B9.1 375187 0% 0% A1 + B9.1 75 + 37537.5 + 187 60% 50% 90% 70%

Example B.XIII

compound Spray amount [g ai / ha] SCPJU SAGPY Measure Colby's E value Measure Colby's E value A1 1837.5 20% 70% B5.4 7537.5 0% 0% A1 + B5.4 18 + 7537.5 + 37.5 50% 20% 100% 70%

Example B.XIV

compound Spray amount [g ai / ha] ECHOR SCPJU Measure Colby's E value Measure Colby's E value A1 7537.5 60% 30% B10.1 18.7537.5 50% 20% A1 + B10.1 75 + 18.7537.5 + 37.5 100% 80% 80% 44%

Example B.XV

compound Spray amount [g ai / ha] SCPJU SAGPY Measure Colby's E value Measure Colby's E value A1 1837.5 20% 70% B4.2 22175 10% 0% A1 + B4.2 18 + 2237.5 + 175 50% 28% 90% 70%

Example B. XVI

compound Spray amount [g ai / ha] SCPJU SAGPY Measure Colby's E value Measure Colby's E value A1 7537.5 50% 70% B12.1 10050 0% 0% A1 + B12.1 75 + 100 37.5 + 50 70% 50% 100% 70%

Example B.XVII

compound Spray amount [g ai / ha] SCPJU SAGPY Measure Colby's E value Measure Colby's E value A1 7518 50% 50% B6.3 7.5 0% 0% A1 + B6.3 75 + 7.518 + 7.5 80% 50% 80% 50%

Claims (9)

A herbicidal composition comprising the following components (A) and (B) in a weight ratio of 1: 2000 to 2000: 1: (A) at least one compound of formula (I) or an agriculturally common salt thereof: Formula I [Wherein, R ¹ is C ₁ -C ₄ -alkyl; R ² is OR ⁶ , SO _m R ⁷ , cyanato, cyano, thiocyanato or halogen; R ³ and R ⁴ are independently hydrogen, halogen, C ₁ -C ₄ -alkyl, halogen-C ₁ -C ₄ -alkyl, cyano, nitro or SO _m R ⁷ ; R ⁵ is O— (CH ₂ ) _a —O— (CH ₂ ) _b —OR ⁷ , C ₃ -C ₈ -cycloalkyloxy, C ₃ -C ₈ -cycloalkyl-C ₁ -C ₄ -alkyloxy, 2-tetrahydrofuranylmethoxy, 3-tetrahydrofuranylmethoxy, 2-tetrahydro-2H-pyranylmethoxy, 2-tetrahydrothienylmethoxy, 2-furanylmethoxy or 2-thienylmethoxy; R ⁶ is hydrogen, C ₁ -C ₄ -alkyl or halogen-C ₁ -C ₄ -alkyl; R ⁷ is C ₁ -C ₄ -alkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, halogen-C ₁ -C ₄ -alkyl, halogen-C ₂ -C ₄ -alkenyl or Halogen-C ₂ -C ₄ -alkynyl; n is 0, 1, 2, 3, 4, 5 or 6; m is 0, 1 or 2; a is 2, 3 or 4; b is 2, 3 or 4] (B) 2,4-D, benzobicyclon, benzofenap, bifenox, cafenstrole, chlorimuron-ethyl, citmethyline (cynmethylin), daimuron, dimethametryn, dithiopyr, etobenzamide, pentrazamide, indanopan, MCPA, oxadione (oxadiazon), piperophos, pyrazosulfuron-ethyl, pyributicarb, pyriftalide (NOJ-100), pyriminobac-methyl One or more herbicide compounds selected from the group consisting of propoxydim and quinoclamine. The method of claim 1, As component (A), R ¹ is methyl; R ² is OR ⁶ ; R ³ and R ⁴ are independently hydrogen, chlorine, fluorine, methyl, trifluoromethyl, cyano, nitro or SO ₂ R ⁷ ; R ⁶ is hydrogen; R ⁷ is methyl or ethyl; n is 0, 1 or 2; m, a and b each comprise a compound of formula (I) Herbicidal composition. The method according to claim 1 or 2, As component (A), R ⁵ is O- (CH ₂ ) _a -O- (CH ₂ ) _b -OR ⁷ , C ₃ -C ₈ -cycloalkyloxy, C ₃ -C ₈ -cycloalkyl-C ₁ -C ₄ -alkyloxy or Comprising a compound of formula (I) which is 2-tetrahydrofuranylmethoxy, Herbicidal composition. The method according to any one of claims 1 to 3, As component (B), benzobicyclone, benzophenaf, biphenox, carfenstrol, cinnamline, dimethamethrin, dithiopyr, etobenzamide, pentazamide, indanophan, oxadione, pipepe A herbicidal composition comprising a herbicide selected from the group consisting of lofos, pyributicab, pyriphthalide, pyriminobac-methyl and quinoclamine. The method of claim 4, wherein One or more herbicides selected from the group consisting of carfenstrol, dithiopyr, etobenzamide, pentrazamide, indanopan, oxadione, pyributicab, pyriphthalide, pyriminobac-methyl and quinoclamine A herbicidal composition comprising. The method according to any one of claims 1 to 5, A herbicidal composition having a combined weight ratio of herbicides (A) and (B) ((A) :( B)) from 1:20 to 20: 1. The method according to any one of claims 1 to 6, A herbicidal composition comprising from 0.1 to 99% by weight of herbicides (A) and (B) and from 99 to 0.1% by weight of formulation aids commonly used for crop protection. Undesired plants, comprising spraying a combination of one or more herbicides (A) and one or more herbicides (B) as defined in any one of claims 1 to 7 on a harmful plant, part thereof or farmland. Control method. Use as a herbicidal composition for the control of undesirable plants of the combination of the herbicides (A) and (B) as defined in claim 1.